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空间排斥与超分子组装:两种紧密相关的苯甲酸 2-(苯并呋喃-2-基)-2-氧代乙酯通过 C-H⋯O 氢键形成的二维平板结构

Steric repulsion and supra-molecular assemblies a two-dimensional plate by C-H⋯O hydrogen bonds in two closely related 2-(benzo-furan-2-yl)-2-oxoethyl benzoates.

作者信息

Then Li Yee, Chidan Kumar C S, Kwong Huey Chong, Win Yip-Foo, Mah Siau Hui, Quah Ching Kheng, Naveen S, Warad Ismail

机构信息

X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.

Department of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahally, Mysuru 570 028, Karnataka, India.

出版信息

Acta Crystallogr E Crystallogr Commun. 2017 Jul 21;73(Pt 8):1227-1231. doi: 10.1107/S2056989017010556. eCollection 2017 Jul 1.

Abstract

2-(Benzo-furan-2-yl)-2-oxoethyl 2-chloro-benzoate, CHClO (I), and 2-(benzo-furan-2-yl)-2-oxoethyl 2-meth-oxy-benzoate, CHO (II), were synthesized under mild conditions. Their chemical and mol-ecular structures were analyzed by spectroscopic and single-crystal X-ray diffraction studies, respectively. These compounds possess different -substituted functional groups on their phenyl rings, thus experiencing extra steric repulsion force within their mol-ecules as the substituent changes from 2-chloro (I) to 2-meth-oxy (II). The crystal packing of compound (I) depends on weak inter-molecular hydrogen bonds and π-π inter-actions. Mol-ecules are related by inversion into centrosymmetric dimers C-H⋯O hydrogen bonds, and further strengthened by π-π inter-actions between furan rings. Conversely, mol-ecules in compound (II) are linked into alternating dimeric chains propagating along the [101] direction, which develop into a two-dimensional plate through extensive inter-molecular hydrogen bonds. These plates are further stabilized by π-π and C-H⋯π inter-actions.

摘要

2-(苯并呋喃-2-基)-2-氧代乙基 2-氯苯甲酸酯(CHClO,I)和 2-(苯并呋喃-2-基)-2-氧代乙基 2-甲氧基苯甲酸酯(CHO,II)在温和条件下合成。分别通过光谱和单晶 X 射线衍射研究对它们的化学结构和分子结构进行了分析。这些化合物在其苯环上具有不同的取代官能团,因此当取代基从 2-氯(I)变为 2-甲氧基(II)时,其分子内会经历额外的空间排斥力。化合物(I)的晶体堆积取决于弱分子间氢键和 π-π 相互作用。分子通过反演形成中心对称二聚体 C-H⋯O 氢键,并通过呋喃环之间的 π-π 相互作用进一步加强。相反,化合物(II)中的分子连接成沿 [101] 方向传播的交替二聚链,通过广泛的分子间氢键形成二维平板。这些平板通过 π-π 和 C-H⋯π 相互作用进一步稳定。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3fd5/5598854/2f0f4ce6e543/e-73-01227-fig1.jpg

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